US3220971A - Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate - Google Patents
Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate Download PDFInfo
- Publication number
- US3220971A US3220971A US141583A US14158361A US3220971A US 3220971 A US3220971 A US 3220971A US 141583 A US141583 A US 141583A US 14158361 A US14158361 A US 14158361A US 3220971 A US3220971 A US 3220971A
- Authority
- US
- United States
- Prior art keywords
- phosphate
- polyethylene
- composition
- octyldiphenyl
- polyethylene containing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000573 polyethylene Polymers 0.000 title description 25
- -1 Polyethylene Polymers 0.000 title description 23
- 239000004698 Polyethylene Substances 0.000 title description 23
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 title description 6
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 title description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- 230000009965 odorless effect Effects 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 4
- 229920013716 polyethylene resin Polymers 0.000 claims description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 21
- 235000021317 phosphate Nutrition 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 229910000423 chromium oxide Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229920001038 ethylene copolymer Polymers 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
Definitions
- This invention relates to the preparation of odorless ethylene polymer and copolymer products.
- An object is to control the formation of persistent odor-generating by-products during the manufacturing process of polyethylene and ethylenecopolymer articles.
- the invention is based on the unexpected discovery that the incorporation of organic phosphates, in the polyethylene or ethylene copolymer compositions, will prevent the formation of odor-generating by products even where the composition contains residual metallic compounds, anti-oxidizers and the like.
- polyethylene will be used to include, where applicable, both polymers of ethylene and copolymers of ethylene with other compounds.
- the invention accordingly comprises the method of producing substantially odorless polyethylene products, which method is characterized by the step of including a small proportion of one or more organic phosphates in the polyethylene composition.
- the invention likewise includes the polyethylene products and shaped articles produced by the specified method.
- the addition of organic phosphate is made prior to the addition of anti-oxidant or other stabilizer agents into the composition.
- the stabilizer agent if soluble, is dissolved or otherwise dispersed in a selected liquid organic phosphate, and the solution or dispersion is added to the polyethylene composition.
- a suitable compatible solvent may be added to a mixture of organic phosphate and stabilizer, and the resulting solution added to the polyethylene.
- the auxiliary solvent may, if desired, be selected sulficiently volatile for ready elimination thereof from the composition.
- organic phosphates including both neutral and acidic salts, may be used according to the invention.
- the phosphates should be selected from within the group of innocuous organic phosphates approved by the competent sanitary agencies.
- an organic phosphate usable according to the invention is octyldiphenyl-phosphate.
- the organic phosphates may be incorporated in the composition in a wide range of proportions for the purposes of the invention. Preferably the proportion is in the range of from 0.002% to 1% by weight of the polyethylene.
- the organic phosphate may be added to the molten polymer, e.g., within a temperature range from 150 to 200 C. by any suitable mechanical or other means, e.g., in a ribbon machine, a roller mill, an internal mixer, or otherwise.
- the phosphates form into complexes with any metal compounds present in the polyethylene composition, and thereby prevent subsequent reaction of said compounds with the polymer and/or the stabilizer and/ or anti-oxidizer agent, even under the high-temperature conditions encountered during the shaping stage.
- Example I A polyethylene composition was prepared by a conventional process with chromium oxide on silica-aluminia carried as a catalyst. The catalyst was retained in the polymer composition, in an amount representing about 0.2% by weight of the polymer. To grams of the polyethylene composition there was incorporated 0.1 g. of the anti-oxidant sold as Ionol (2,6-ditert-butyl-4- methyl-phenol), using a roller mill at C. The resulting stabilized polymer composition was ground and moulded into plates in a molding press in which the press pot was heated to about 250 C.
- the anti-oxidant sold as Ionol (2,6-ditert-butyl-4- methyl-phenol
- the resulting plates had a disagreeable odor which persisted for many weeks, especially when stored in a confined space.
- Example 11 A polyethylene composition was similarly prepared with chromium oxide on silica-alumina as a catalyst. The catalyst was retained in the composition, in an amount of about 0.2% by weight of the polymer. To 100 grams of the composition there was then incorporated according to the invention 0.25 g. octyldiphenylphosphate, using a roller mill at 150 C. Thereafter 0.1 grams of Ionol anti-oxidant were incorporated by the same procedure. The resulting polymer composition was ground and moulded into plates by the same procedure as in Example I.
- the plates were found not to possess any perceptible smell even when stored in confined conditions.
- Example III In an internal mixer operated at a temperature of 150 C. 0.5 g. octyldiphenylphosphate was incorporated in 100 g. of an ethylene-butene-l copolymer containing 0.5 g. chromium oxide on silica-alumina as a catalyst. 0.1 g. of Ionol antioxidant was then incorporated in the mix. Plates were moulded from the composition as above, and were found to be completely odorless even under confined conditions.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR856501A FR1292337A (fr) | 1961-03-22 | 1961-03-22 | Procédé d'obtention de polyéthylène inodore et produit ainsi obtenu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3220971A true US3220971A (en) | 1965-11-30 |
Family
ID=8751462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US141583A Expired - Lifetime US3220971A (en) | 1961-03-22 | 1961-09-29 | Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3220971A (fr) |
| FR (1) | FR1292337A (fr) |
| GB (1) | GB986197A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5473842A (en) * | 1977-11-25 | 1979-06-13 | Mitsubishi Petrochem Co Ltd | Polyolefin resin composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2825721A (en) * | 1953-01-27 | 1958-03-04 | Phillips Petroleum Co | Polymers and production thereof |
| US2952658A (en) * | 1955-12-19 | 1960-09-13 | Dow Chemical Co | Linear polyethylene stabilized with alkali phosphates |
| US2980964A (en) * | 1956-01-14 | 1961-04-25 | Distillers Co Yeast Ltd | Linear polyethylene films of improved transparency and method of making same |
| US2985617A (en) * | 1955-09-02 | 1961-05-23 | Monsanto Chemicals | Stabilized polymer of 2 to 3 carbon atoms |
| US3020258A (en) * | 1959-08-31 | 1962-02-06 | Phillips Petroleum Co | Odor inhibitors for olefin polymers |
-
1961
- 1961-03-22 FR FR856501A patent/FR1292337A/fr not_active Expired
- 1961-09-26 GB GB34524/61A patent/GB986197A/en not_active Expired
- 1961-09-29 US US141583A patent/US3220971A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2825721A (en) * | 1953-01-27 | 1958-03-04 | Phillips Petroleum Co | Polymers and production thereof |
| US2985617A (en) * | 1955-09-02 | 1961-05-23 | Monsanto Chemicals | Stabilized polymer of 2 to 3 carbon atoms |
| US2952658A (en) * | 1955-12-19 | 1960-09-13 | Dow Chemical Co | Linear polyethylene stabilized with alkali phosphates |
| US2980964A (en) * | 1956-01-14 | 1961-04-25 | Distillers Co Yeast Ltd | Linear polyethylene films of improved transparency and method of making same |
| US3020258A (en) * | 1959-08-31 | 1962-02-06 | Phillips Petroleum Co | Odor inhibitors for olefin polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1292337A (fr) | 1962-05-04 |
| GB986197A (en) | 1965-03-17 |
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